Syntheses of 1,2,3-triazole-BODIPYs bearing up to three carbohydrate unitsElectronic supplementary information (ESI) available: It contains 1H, 11B and 13C NMR spectra for all BODIPYs. CCDC 1580552 and 1580553. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8nj00041g
A series of BODIPYs bearing one ( 4b,c ), two ( 6a ) or three ( 3b ) glucose units attached to the meso (8) and the boron atom positions were synthesized using a Cu( i )-catalyzed Huisgen cycloaddition reaction. The resulting 1,2,3-triazole-BODIPYs were characterized by 1 H, 13 C and 11 B NMR, HRMS,...
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| creator | Nguyen, Alex L Griffin, Kaitlin E Zhou, Zehua Fronczek, Frank R Smith, Kevin M Vicente, M. Graça H |
| description | A series of BODIPYs bearing one (
4b,c
), two (
6a
) or three (
3b
) glucose units attached to the
meso
(8) and the boron atom positions were synthesized using a Cu(
i
)-catalyzed Huisgen cycloaddition reaction. The resulting 1,2,3-triazole-BODIPYs were characterized by
1
H,
13
C and
11
B NMR, HRMS, and in the case of
4a
and
4b
by X-ray crystallography. Triazole-BODIPYs
3b
,
4b
and
6a
were highly permeable in cells and non-toxic to human HEp2 cells, both in the dark and upon light irradiation (IC
50
> 100 μM). The time-dependent cellular uptake increased with the increase number of glucose units.
BODIPYs bearing up to three glucose units were synthesized and their cytotoxicity and uptake investigated in human HEp2 cells. |
| doi_str_mv | 10.1039/c8nj00041g |
| format | Article |
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4b,c
), two (
6a
) or three (
3b
) glucose units attached to the
meso
(8) and the boron atom positions were synthesized using a Cu(
i
)-catalyzed Huisgen cycloaddition reaction. The resulting 1,2,3-triazole-BODIPYs were characterized by
1
H,
13
C and
11
B NMR, HRMS, and in the case of
4a
and
4b
by X-ray crystallography. Triazole-BODIPYs
3b
,
4b
and
6a
were highly permeable in cells and non-toxic to human HEp2 cells, both in the dark and upon light irradiation (IC
50
> 100 μM). The time-dependent cellular uptake increased with the increase number of glucose units.
BODIPYs bearing up to three glucose units were synthesized and their cytotoxicity and uptake investigated in human HEp2 cells.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/c8nj00041g</identifier><language>eng</language><creationdate>2018-05</creationdate><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Nguyen, Alex L</creatorcontrib><creatorcontrib>Griffin, Kaitlin E</creatorcontrib><creatorcontrib>Zhou, Zehua</creatorcontrib><creatorcontrib>Fronczek, Frank R</creatorcontrib><creatorcontrib>Smith, Kevin M</creatorcontrib><creatorcontrib>Vicente, M. Graça H</creatorcontrib><title>Syntheses of 1,2,3-triazole-BODIPYs bearing up to three carbohydrate unitsElectronic supplementary information (ESI) available: It contains 1H, 11B and 13C NMR spectra for all BODIPYs. CCDC 1580552 and 1580553. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8nj00041g</title><description>A series of BODIPYs bearing one (
4b,c
), two (
6a
) or three (
3b
) glucose units attached to the
meso
(8) and the boron atom positions were synthesized using a Cu(
i
)-catalyzed Huisgen cycloaddition reaction. The resulting 1,2,3-triazole-BODIPYs were characterized by
1
H,
13
C and
11
B NMR, HRMS, and in the case of
4a
and
4b
by X-ray crystallography. Triazole-BODIPYs
3b
,
4b
and
6a
were highly permeable in cells and non-toxic to human HEp2 cells, both in the dark and upon light irradiation (IC
50
> 100 μM). The time-dependent cellular uptake increased with the increase number of glucose units.
BODIPYs bearing up to three glucose units were synthesized and their cytotoxicity and uptake investigated in human HEp2 cells.</description><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFkM1PwkAQxavRREQv3k3GmyYUO_1A4EiB0INixIsnMrRbumbZbXYXk_rXuwKJBxM9zWT2N2_eW8-7wqCLQTS4z_vyPQiCGNfHXguj3sAfhD08cT3GsR8kce_MOzfGMYgPPWwdhYtG2ooZZkCVgJ2wE_lWc_pUgvmj-Th7fjOwYqS5XMO2BqvAVpoxyEmvVNUUmiyDreTWTATLrVaS52C2dS3YhklLugEuS6U3ZLmScDtZZHdAH8QFrQQbQmYhV47j0gDOOoA4ApIFYJTC0-MLmPpblcBJAAkBB09dSNNxCpj0gyQJ9xu7PurC1KHuzG6Y68ZYt6fWmurKWSvIknMEaTYFxykXXgP7sb63CsZFHM-zIfz-2QvvtCRh2OWhtr3r6eQ1nfna5Mta843LvPzBo7Z389f7si7K6D-NL8LpkxM</recordid><startdate>20180514</startdate><enddate>20180514</enddate><creator>Nguyen, Alex L</creator><creator>Griffin, Kaitlin E</creator><creator>Zhou, Zehua</creator><creator>Fronczek, Frank R</creator><creator>Smith, Kevin M</creator><creator>Vicente, M. Graça H</creator><scope/></search><sort><creationdate>20180514</creationdate><title>Syntheses of 1,2,3-triazole-BODIPYs bearing up to three carbohydrate unitsElectronic supplementary information (ESI) available: It contains 1H, 11B and 13C NMR spectra for all BODIPYs. CCDC 1580552 and 1580553. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8nj00041g</title><author>Nguyen, Alex L ; Griffin, Kaitlin E ; Zhou, Zehua ; Fronczek, Frank R ; Smith, Kevin M ; Vicente, M. Graça H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c8nj00041g3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nguyen, Alex L</creatorcontrib><creatorcontrib>Griffin, Kaitlin E</creatorcontrib><creatorcontrib>Zhou, Zehua</creatorcontrib><creatorcontrib>Fronczek, Frank R</creatorcontrib><creatorcontrib>Smith, Kevin M</creatorcontrib><creatorcontrib>Vicente, M. Graça H</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nguyen, Alex L</au><au>Griffin, Kaitlin E</au><au>Zhou, Zehua</au><au>Fronczek, Frank R</au><au>Smith, Kevin M</au><au>Vicente, M. Graça H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses of 1,2,3-triazole-BODIPYs bearing up to three carbohydrate unitsElectronic supplementary information (ESI) available: It contains 1H, 11B and 13C NMR spectra for all BODIPYs. CCDC 1580552 and 1580553. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8nj00041g</atitle><date>2018-05-14</date><risdate>2018</risdate><volume>42</volume><issue>1</issue><spage>8241</spage><epage>8246</epage><pages>8241-8246</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>A series of BODIPYs bearing one (
4b,c
), two (
6a
) or three (
3b
) glucose units attached to the
meso
(8) and the boron atom positions were synthesized using a Cu(
i
)-catalyzed Huisgen cycloaddition reaction. The resulting 1,2,3-triazole-BODIPYs were characterized by
1
H,
13
C and
11
B NMR, HRMS, and in the case of
4a
and
4b
by X-ray crystallography. Triazole-BODIPYs
3b
,
4b
and
6a
were highly permeable in cells and non-toxic to human HEp2 cells, both in the dark and upon light irradiation (IC
50
> 100 μM). The time-dependent cellular uptake increased with the increase number of glucose units.
BODIPYs bearing up to three glucose units were synthesized and their cytotoxicity and uptake investigated in human HEp2 cells.</abstract><doi>10.1039/c8nj00041g</doi><tpages>6</tpages></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Syntheses of 1,2,3-triazole-BODIPYs bearing up to three carbohydrate unitsElectronic supplementary information (ESI) available: It contains 1H, 11B and 13C NMR spectra for all BODIPYs. CCDC 1580552 and 1580553. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8nj00041g |
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